S-[11beta,17-dihydroxypregn-4-ene-3,20-dione] 21-(thiopivalate)

Chemical Properties

Pale Yellow Solid

Originator

Pivalone,Jouveinal,France,1978

Uses

Free thiol in chemoaffinity labeling.

Uses

Tixocortol 21-Pivalate is an anti-inflammatory agent. Tixocortol 21-Pivalate is used in fluorescent chemoaffinity labeling.

Uses

Anti-inflammatory. Used in fluorescent chemoaffinity labeling.

Definition

ChEBI: The pivalate thioester of tixocortol.

Manufacturing Process

In a reactor of 50 liters, sodium S-thiopivalate is prepared from 100 g of S_x0002_thiopivalic acid (0.844 mol), 214 cc of solution of sodium methylate, 3.95 M (0.844 mol) in 25 liters of anhydrous acetone.
There are then added 285 g (0.603 mol) of dihydroxy-11β,17α-iodo-21-dioxo- 3,20-pregnene-4 and the mixture is brought up to the acetone reflux for two hours. The solvent is eliminated by distillation under vacuum until there is obtained a syrupy residue which is poured into 10 liters of iced water. The insoluble part is filtered and dried under vacuum.
The crude product is purified by recrystallization from ethanol; weight: 250 g; yield: 89.5%.

Therapeutic Function

Antiinflammatory

Contact allergens

Tixocortol 21-pivalate is a 21-ester of tixocortol, widely used in topical treatments. It can induce severe allergic contact dermatitis. This corticosteroid is a marker of the allergenic A group that includes molecules without major substitution on the D cycle (no C 16 methylation, no C 17 side chain). A short-chain C 21 ester is possible. Molecules are cloprednol, cortisone, fludrocortisone, fluorometholone, hydrocortisone, methylprednisolone, methylprednisone, prednisolone, prednisone, tixocor- tol, and their C 21 esters (acetate, caproate or hexanoate, phosphate, pivalate or trimethylacetate, succinate or hemisuccinate, m-sulfobenzoate).